DE19531138A1 - Alkenyl-benzoylguanidin-Derivate - Google Patents
Alkenyl-benzoylguanidin-DerivateInfo
- Publication number
- DE19531138A1 DE19531138A1 DE19531138A DE19531138A DE19531138A1 DE 19531138 A1 DE19531138 A1 DE 19531138A1 DE 19531138 A DE19531138 A DE 19531138A DE 19531138 A DE19531138 A DE 19531138A DE 19531138 A1 DE19531138 A1 DE 19531138A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- diaminomethylene
- benzamide
- methylsulfonyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 Alkenyl benzoylguanidine derivatives Chemical class 0.000 title claims description 90
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 45
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 22
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 9
- CGVDKYPZVVFXKO-UHFFFAOYSA-N 4-cyclopent-2-en-1-yl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(C2C=CCC2)=C1S(C)(=O)=O CGVDKYPZVVFXKO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000006317 isomerization reaction Methods 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 206010061216 Infarction Diseases 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 230000007574 infarction Effects 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000003449 preventive effect Effects 0.000 claims description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 3
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 3
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 230000006793 arrhythmia Effects 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- MCDRRAPMQSZBJE-UHFFFAOYSA-N n-(diaminomethylidene)-4-ethenyl-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(C=C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N MCDRRAPMQSZBJE-UHFFFAOYSA-N 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 125000006239 protecting group Chemical group 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 238000010626 work up procedure Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 235000019799 monosodium phosphate Nutrition 0.000 description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
- 229910000162 sodium phosphate Inorganic materials 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- ZKTANDGIDFMKFE-UHFFFAOYSA-N 4-cyclopent-2-en-1-yl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(C2C=CCC2)=C1S(C)(=O)=O ZKTANDGIDFMKFE-UHFFFAOYSA-N 0.000 description 3
- MGIJKWANBMHMLH-UHFFFAOYSA-N 4-cyclopent-3-en-1-yl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(C2CC=CC2)=C1S(C)(=O)=O MGIJKWANBMHMLH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 238000007341 Heck reaction Methods 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
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- FZCUNTIKJXXWCL-UHFFFAOYSA-N 4-but-3-en-2-yl-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC1=CC(C(C)C=C)=C(S(C)(=O)=O)C=C1C(Cl)=O FZCUNTIKJXXWCL-UHFFFAOYSA-N 0.000 description 2
- YWJWEDPBASVAQY-UHFFFAOYSA-N 4-but-3-en-2-yl-2-methyl-5-(trifluoromethyl)benzoyl chloride Chemical compound C=CC(C)C1=CC(C)=C(C(Cl)=O)C=C1C(F)(F)F YWJWEDPBASVAQY-UHFFFAOYSA-N 0.000 description 2
- PWOPRQBEOAZKKJ-UHFFFAOYSA-N 4-but-3-en-2-yl-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound C=CC(C)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O PWOPRQBEOAZKKJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Gastroenterology & Hepatology (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19531138A DE19531138A1 (de) | 1995-08-24 | 1995-08-24 | Alkenyl-benzoylguanidin-Derivate |
| TW085109043A TW401390B (en) | 1995-08-24 | 1996-07-24 | Alkenyl-benzoylguanidine derivatives |
| SI9630293T SI0760365T1 (en) | 1995-08-24 | 1996-08-16 | Alkenyl-benzoylguanidines |
| ES96113175T ES2154370T3 (es) | 1995-08-24 | 1996-08-16 | Alquenil-benzoilguanidinas. |
| PT96113175T PT760365E (pt) | 1995-08-24 | 1996-08-16 | Alcenil-benzoilguanidinas |
| EP96113175A EP0760365B1 (de) | 1995-08-24 | 1996-08-16 | Alkenyl-Benzoylguanidine |
| DK96113175T DK0760365T3 (da) | 1995-08-24 | 1996-08-16 | Alkenyl-benzoylguanidiner |
| CZ19962436A CZ288609B6 (cs) | 1995-08-24 | 1996-08-16 | Derivát alkenylbenzoylguanidinu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje |
| DE59606269T DE59606269D1 (de) | 1995-08-24 | 1996-08-16 | Alkenyl-Benzoylguanidine |
| AT96113175T ATE198470T1 (de) | 1995-08-24 | 1996-08-16 | Alkenyl-benzoylguanidine |
| AU62148/96A AU718430B2 (en) | 1995-08-24 | 1996-08-19 | Alkenyl-benzoylguanidine derivatives |
| UA96083321A UA41393C2 (uk) | 1995-08-24 | 1996-08-21 | Похідні алкенілбензоїлгуанідину, спосіб їх одержання, фармацевтична композиція, спосіб її одержання |
| SK1081-96A SK281919B6 (sk) | 1995-08-24 | 1996-08-21 | Derivát alkenylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje |
| MX9603568A MX9603568A (es) | 1995-08-24 | 1996-08-22 | Derivados de la alquenil-benzoilguanidina. |
| BR9603508A BR9603508A (pt) | 1995-08-24 | 1996-08-22 | Derivados de alquenil-benzoilguanidina |
| CA002183937A CA2183937A1 (en) | 1995-08-24 | 1996-08-22 | Alkenyl-benzoylguanidine derivatives |
| CN96111527A CN1063438C (zh) | 1995-08-24 | 1996-08-22 | 链烯基-苯甲酰胍衍生物及其制备和用途 |
| JP8239937A JPH09124583A (ja) | 1995-08-24 | 1996-08-23 | アルケニル−ベンゾイルグアニジン誘導体 |
| ZA967204A ZA967204B (en) | 1995-08-24 | 1996-08-23 | Alkenyl-benzoylguanidine derivatives |
| NO963525A NO306991B1 (no) | 1995-08-24 | 1996-08-23 | Alkenylbenzoylguanidinderivater, farmasoeytiske preparater som inneholder slike, samt anvendelse av forbindelsene til fremstilling av legemidler |
| HU9602331A HUP9602331A3 (en) | 1995-08-24 | 1996-08-23 | Alkenyl-benzoyl-guanidine derivatives, pharmaceutical compns. contg. the said compds., process for preparing them and the use of the compds. |
| ARP960104089A AR004680A1 (es) | 1995-08-24 | 1996-08-23 | Derivados de la alquenil-benzoilguanidina, procedimiento para prepararlos y preparaciones farmaceuticas que los contienen. |
| KR1019960035109A KR970010739A (ko) | 1995-08-24 | 1996-08-23 | 알케닐-벤조일구아니딘 유도체 |
| US08/701,993 US5731351A (en) | 1995-08-24 | 1996-08-23 | Alkenyl-benzoylguanidine derivatives |
| PL96315800A PL315800A1 (en) | 1995-08-24 | 1996-08-23 | Novel derivatives of alkenyl benzoyloguanidine, method of obtaining them as well as pharmaceutic preparation and method of obtaining same |
| GR20010400323T GR3035481T3 (en) | 1995-08-24 | 2001-02-28 | Alkenyl-benzoylguanidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19531138A DE19531138A1 (de) | 1995-08-24 | 1995-08-24 | Alkenyl-benzoylguanidin-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19531138A1 true DE19531138A1 (de) | 1997-02-27 |
Family
ID=7770272
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19531138A Withdrawn DE19531138A1 (de) | 1995-08-24 | 1995-08-24 | Alkenyl-benzoylguanidin-Derivate |
| DE59606269T Expired - Fee Related DE59606269D1 (de) | 1995-08-24 | 1996-08-16 | Alkenyl-Benzoylguanidine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59606269T Expired - Fee Related DE59606269D1 (de) | 1995-08-24 | 1996-08-16 | Alkenyl-Benzoylguanidine |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5731351A (cs) |
| EP (1) | EP0760365B1 (cs) |
| JP (1) | JPH09124583A (cs) |
| KR (1) | KR970010739A (cs) |
| CN (1) | CN1063438C (cs) |
| AR (1) | AR004680A1 (cs) |
| AT (1) | ATE198470T1 (cs) |
| AU (1) | AU718430B2 (cs) |
| BR (1) | BR9603508A (cs) |
| CA (1) | CA2183937A1 (cs) |
| CZ (1) | CZ288609B6 (cs) |
| DE (2) | DE19531138A1 (cs) |
| DK (1) | DK0760365T3 (cs) |
| ES (1) | ES2154370T3 (cs) |
| GR (1) | GR3035481T3 (cs) |
| HU (1) | HUP9602331A3 (cs) |
| MX (1) | MX9603568A (cs) |
| NO (1) | NO306991B1 (cs) |
| PL (1) | PL315800A1 (cs) |
| PT (1) | PT760365E (cs) |
| SI (1) | SI0760365T1 (cs) |
| SK (1) | SK281919B6 (cs) |
| TW (1) | TW401390B (cs) |
| UA (1) | UA41393C2 (cs) |
| ZA (1) | ZA967204B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4328352A1 (de) * | 1993-08-24 | 1995-03-02 | Hoechst Ag | Substituierte N,N'-Di-benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19608161A1 (de) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| IL126276A0 (en) * | 1997-09-24 | 1999-05-09 | Hoechst Marion Roussel De Gmbh | The use of an inhibitor of the na+/H+ exchanger for the production of a medicament for the treatment or prophylaxis of disorders of the central nervous system |
| BR9915667A (pt) * | 1998-11-26 | 2001-08-14 | Merck Patent Gmbh | Uso de benzoilguanidinas para o tratamento de diabetes melitus não dependente de insulina |
| DE19929857A1 (de) * | 1999-06-29 | 2001-01-04 | Merck Patent Gmbh | Verfahren zur Herstellung eines 4-(Pyrrol-1-yl)-benzoylguanidinderivates |
| NZ610449A (en) * | 2010-11-05 | 2014-12-24 | Zhejiang Hisun Pharm Co Ltd | Benzamide derivative with anticancer activity and preparation method and use thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3929582A1 (de) * | 1989-09-06 | 1991-03-07 | Hoechst Ag | Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament |
| ATE144248T1 (de) * | 1992-07-01 | 1996-11-15 | Hoechst Ag | 3,4,5-substituierte benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament oder diagnostikum sowie sie enthaltendes medikament |
| DE4318756A1 (de) * | 1993-06-05 | 1994-12-08 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4328869A1 (de) * | 1993-08-27 | 1995-03-02 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4417004A1 (de) * | 1994-05-13 | 1995-11-16 | Hoechst Ag | Perfluoralkyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| IL114670A0 (en) * | 1994-08-05 | 1995-11-27 | Fujisawa Pharmaceutical Co | Guanidine derivatives pharmaceutical compositions containing the same and processes for the preparation thereof |
| DE4430916A1 (de) * | 1994-08-31 | 1996-03-07 | Merck Patent Gmbh | Alkyl-benzoylguanidin-Derivate |
-
1995
- 1995-08-24 DE DE19531138A patent/DE19531138A1/de not_active Withdrawn
-
1996
- 1996-07-24 TW TW085109043A patent/TW401390B/zh not_active IP Right Cessation
- 1996-08-16 AT AT96113175T patent/ATE198470T1/de not_active IP Right Cessation
- 1996-08-16 SI SI9630293T patent/SI0760365T1/xx unknown
- 1996-08-16 PT PT96113175T patent/PT760365E/pt unknown
- 1996-08-16 DK DK96113175T patent/DK0760365T3/da active
- 1996-08-16 ES ES96113175T patent/ES2154370T3/es not_active Expired - Lifetime
- 1996-08-16 EP EP96113175A patent/EP0760365B1/de not_active Expired - Lifetime
- 1996-08-16 DE DE59606269T patent/DE59606269D1/de not_active Expired - Fee Related
- 1996-08-16 CZ CZ19962436A patent/CZ288609B6/cs not_active IP Right Cessation
- 1996-08-19 AU AU62148/96A patent/AU718430B2/en not_active Ceased
- 1996-08-21 SK SK1081-96A patent/SK281919B6/sk unknown
- 1996-08-21 UA UA96083321A patent/UA41393C2/uk unknown
- 1996-08-22 MX MX9603568A patent/MX9603568A/es not_active IP Right Cessation
- 1996-08-22 CN CN96111527A patent/CN1063438C/zh not_active Expired - Fee Related
- 1996-08-22 CA CA002183937A patent/CA2183937A1/en not_active Abandoned
- 1996-08-22 BR BR9603508A patent/BR9603508A/pt active Search and Examination
- 1996-08-23 AR ARP960104089A patent/AR004680A1/es not_active Application Discontinuation
- 1996-08-23 ZA ZA967204A patent/ZA967204B/xx unknown
- 1996-08-23 HU HU9602331A patent/HUP9602331A3/hu unknown
- 1996-08-23 PL PL96315800A patent/PL315800A1/xx unknown
- 1996-08-23 US US08/701,993 patent/US5731351A/en not_active Expired - Fee Related
- 1996-08-23 KR KR1019960035109A patent/KR970010739A/ko not_active Ceased
- 1996-08-23 JP JP8239937A patent/JPH09124583A/ja active Pending
- 1996-08-23 NO NO963525A patent/NO306991B1/no not_active IP Right Cessation
-
2001
- 2001-02-28 GR GR20010400323T patent/GR3035481T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR9603508A (pt) | 1998-05-12 |
| HUP9602331A2 (en) | 1997-05-28 |
| UA41393C2 (uk) | 2001-09-17 |
| HU9602331D0 (en) | 1996-10-28 |
| KR970010739A (ko) | 1997-03-27 |
| PL315800A1 (en) | 1997-03-03 |
| EP0760365B1 (de) | 2001-01-03 |
| AR004680A1 (es) | 1999-03-10 |
| ATE198470T1 (de) | 2001-01-15 |
| SI0760365T1 (en) | 2001-08-31 |
| DE59606269D1 (de) | 2001-02-08 |
| TW401390B (en) | 2000-08-11 |
| ZA967204B (en) | 1997-03-03 |
| AU6214896A (en) | 1997-02-27 |
| ES2154370T3 (es) | 2001-04-01 |
| EP0760365A3 (de) | 1998-07-08 |
| CN1063438C (zh) | 2001-03-21 |
| CA2183937A1 (en) | 1997-02-25 |
| NO963525D0 (no) | 1996-08-23 |
| CN1150947A (zh) | 1997-06-04 |
| GR3035481T3 (en) | 2001-05-31 |
| JPH09124583A (ja) | 1997-05-13 |
| SK108196A3 (en) | 1997-06-04 |
| SK281919B6 (sk) | 2001-09-11 |
| US5731351A (en) | 1998-03-24 |
| NO963525L (no) | 1997-02-25 |
| HUP9602331A3 (en) | 1999-12-28 |
| PT760365E (pt) | 2001-05-31 |
| EP0760365A2 (de) | 1997-03-05 |
| CZ288609B6 (cs) | 2001-07-11 |
| AU718430B2 (en) | 2000-04-13 |
| MX9603568A (es) | 1997-06-28 |
| DK0760365T3 (da) | 2001-05-14 |
| CZ243696A3 (en) | 1997-03-12 |
| NO306991B1 (no) | 2000-01-24 |
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| 8139 | Disposal/non-payment of the annual fee |